Diethylamine → 4-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(diethylamino)ethoxy)phenyl)but-1-enyl)phenol

HRID 626263Notes

Reaction equation

HRID 626263 reaction equation
[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:30][CH3:31])=[C:12]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:13]3[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH2:21]Cl)=[CH:15][CH:14]=3)=[CH:7][C:5]=2[CH:6]=1.[CH2:32]([NH:34][CH2:35][CH3:36])[CH3:33]>CO>[Cl:1][C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([C:11]([CH2:30][CH3:31])=[C:12]([C:23]3[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=3)[C:13]3[CH:14]=[CH:15][C:16]([O:19][CH2:20][CH2:21][N:34]([CH2:35][CH3:36])[CH2:32][CH3:33])=[CH:17][CH:18]=3)=[CH:7][C:5]=2[CH:6]=1

Participants

4

Reactant 2

HCID 8021DiethylamineHCID 1239950204-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol

Product 1

HCID 726804774-(2-(2-Chlorobenzofuran-5-yl)-1-(4-(2-(diethylamino)ethoxy)phenyl)but-1-enyl)phenolYield 81%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

According to the same procedure as example 1, step E described, 4-(2-(2-chlorobenzofuran-5-yl)-1-(4-(2-chloroethoxy)phenyl)but-1-enyl)phenol (70 mg, 1.0 eq, made by example 11, step D) was reacted with diethylamine (3 mL) in MeOH (8 mL) under reflux to give the desired product (61 mg, 81%, Z/E=1/1.25) as a brown solid. 1HNMR (400 MHz, CDCl3) δ 7.23 (s, 1H), 7.20 (d, J=8.4 Hz, 1H), 7.12 & 7.09 (d, J=8.8 Hz, 2H), 7.00 & 6.99 (d, J=8.4 Hz, 1H), 6.83 & 6.80 (d, J=8.8 Hz, 2H), 6.71 & 6.69 (d, J=8.4 Hz, 2H), 6.45 (s, 1H), 6.43 (d, J=8.8 Hz, 2H), 4.08 & 3.90 (t, J=5.8 Hz, 2H), 2.92 & 2.80 (t, J=5.8 Hz, 2H), 2.69 & 2.62 (q, J=7.0 Hz, 4H), 2.50 (q, J=7.6 Hz, 2H), 1.10 & 1.04 (q, J=7.2 Hz, 6H), 0.91 (t, J=7.6 Hz, 3H); m/z=490[M+1]+.

Workup

  1. temperatureunder reflux

Sources & evidence

ORD record
ord-24b6d4e67b234ccf863347c75cc5d1a3
Source dataset
uspto-grants-2016_04
Patent number
US09309211B2

Reaction notes

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